Apartment vacation rentals in Wrigleyville

An inviting living space features large windows allowing natural light, framed by exposed brick walls. A round dining table is surrounded by modern chairs, while a comfortable sectional sofa is positioned near a cozy fireplace, enhancing the warm ambience. Stylish decor elements add character to the room.

4.97 out of 5 average rating, 243 reviews

Modern vintage chic steps from Wrigley Field!

Vintage touches and modern updates in the heart of Wrigleyville! Includes off street parking. Close enough to see Wrigley Field from the building, yet the block is charming and quiet. Close to the lake and Boystown. The vintage DNA is beautifully respected while updates provide the modern amenities you expect when traveling. Large deck. You will love the exposed brick and original millwork while enjoying huge new windows, an open floor plan, chef's kitchen, stylish decor, and spa like bathroom.

Apartment in Roscoe Village

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.95 out of 5 average rating, 222 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

A living room features a large bay window with multiple panes, offering a view of greenery outside. A comfortable sofa is adorned with colorful pillows, complemented by a contemporary armchair and side tables. Warm light is provided by a nearby lamp.

4.98 out of 5 average rating, 270 reviews

North Side Near Wrigley Lakeview Walk Everywhere!!

Located on a beautiful tree lined street one block from the thriving Southport Corridor, one of the hottest neighborhoods in Chicago. You'll love the convenience of being just steps from the Southport Brown Line "L" Stop, you can see the City without ever needing to drive. Steps to outstanding restaurants, bars and shopping. Going to Wrigley Field? Enjoy a 10 minute walk down some of the most beautiful streets in Chicago. Ideal for families seeking comfort, style and a convenient location.

A vibrant garden is visible with two blue Adirondack chairs placed on lush green grass. Potted plants are scattered on a table in the foreground. In the background, a domestic cat can be seen among greenery and flowering plants, creating a serene outdoor setting.

4.97 out of 5 average rating, 332 reviews

The Garden on Wayne

Located in one of the top 3 neighborhoods in Chicago, a great spot for a couple, a small family, business travel or a weekend with the girls. Close to high end shopping, a world famous and historic theatre and dozens of restaurants, our quaint garden apartment offers a quiet spot in a great area for weekending - and is also the midpoint between O'Hare and Downtown. The Lakefront is a quick 20-minute walk; the Lincoln Park Zoo is 20 minutes in an Uber. Please see below for further detail

A spacious living room is highlighted by a large sectional sofa adorned with colorful cushions. A flat-screen television sits opposite a cozy fireplace, framed by light-colored bricks. Two windows allow natural light to fill the room, enhancing the relaxed ambiance.

5 out of 5 average rating, 117 reviews

Steps away from Wrigley Field!!

The Wrigley Home is a newly renovated 2-bedroom with spacious living room & dining room. Ideal location for groups & families as this family-friendly neighborhood is walking distance to train stops (Addison- Red Line & Southport- Brown Line), retail shops, bars, restaurants, parks, and more! You will feel like home with a large sofa, fireplace, dining room table, brand new kitchen appliances, the amenities of home, pack and play, high chair, stroller, toys, backyard for grilling, etc.

A bright bedroom features a spacious bed dressed in white linens, surrounded by vibrant, tropical-inspired wallpaper. Two windows allow natural light to fill the room, accented by subtle shades and animal motifs. A small red chair is positioned near the bed, adding a playful touch.

4.99 out of 5 average rating, 321 reviews

A Whimsical Fairy-tale Loft in Ravenswood Chicago

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

A comfortable sitting area is furnished with a light gray sofa, a cozy armchair, and a wooden coffee table. A large window allows natural light to brighten the room, featuring playful blue and white accents. A vintage Cubs banner and framed artwork add a local touch.

4.97 out of 5 average rating, 136 reviews

Charming suite 3 blocks from Wrigley Field

Your Wrigleyville get-away destination awaits! Spend a fun, baseball themed weekend within 3 blocks of Wrigley Field on this quaint neighborhood block. Walking distance to dozens of bars and restaurants in Lakeview & 3 blocks from the "El" CTA train Brown & Red lines. This suite sleeps 4 people comfortably and is perfect for families. A full kitchen, desk, coffee station, Wifi, and smart TV can be your home away from home. Book your weekend now for the next homestand or concert!

An elegant stone entrance is framed by lush green ivy, leading to a wooden door beneath a decorative awning. A charming fountain, featuring three tiers, adds a serene element to the outdoor area, surrounded by abundant foliage and creating a peaceful environment.

4.99 out of 5 average rating, 139 reviews

CASA NEWPORT

Second floor, one bedroom apartment, with an additional queen pullout couch located in a beautiful historic district in Lakeview. Just steps away from Halsted street/Boystown/Wrigley field. Conveniently located to shopping, restaurants, subway (EL) and grocery stores. Close to lakefront, jogging path and bike path. Complementary street parking passes available. The apartment does NOT have airconditioning. It does have a window unit in the bedroom from April to September.

Apartment in Lincoln Square

A cozy living area features two dark leather sofas, a marble-topped coffee table, and a flat-screen television. Natural light enters through a window with blinds, while a warm brick wall adds character. A decorative console table is positioned along the side of the room.

4.91 out of 5 average rating, 274 reviews

Newly Rehabbed! 2br with Vintage Charm

Our 2 bed garden apartment in Ravenswood will be the ideal home base for your stay! Located in one of Chicago's vibrant Northside neighborhoods, you’ll experience local charm outside your door. The home has space for 5 and a newly renovated kitchen, though you may not have time to cook with many family-owned restaurants within walking distance! The Montrose Brown Line is only 3 blocks away, taking you downtown in 30 minutes and Lakeview/Lincoln Park in even less.

A living room features warm yellow walls and hardwood flooring. A cozy sofa faces a decorative fireplace set into a red brick mantle. Two chairs and a small table are positioned near a large window dressed with light curtains, allowing natural light to fill the space.

4.94 out of 5 average rating, 139 reviews

The Wrigley Flats | Chicago Vacation Rental

The Wrigley Flats is a unique Chicago vacation rental located 4 blocks south of Wrigley Field in city’s most sought after north side neighborhood---Wrigleyville! Our 3 bedroom | 1 bathroom flat can be rented for a weekend getaway, a week long vacation or an extended stay. Close proximity to Chicago’s lakefront, vibrant nightlife, the eclectic dining scene & of course Wrigley Field; it’s no wonder visitors flock here to get a taste of something amazing!

A bright living area features large bay windows with natural light filtering through. A white sofa is complemented by decorative pillows and a coffee table adorned with flowers. A mirror adorns the wall, enhancing the sense of space and light.

4.93 out of 5 average rating, 242 reviews

Penthouse Near Wrigley Field

This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

An open-concept living area is featured, showcasing a dark sofa complemented by light-colored pillows. A round coffee table sits on a patterned rug, and a dining area for four is visible nearby. Modern kitchen appliances are neatly arranged against the backdrop of sleek cabinetry, with natural light flowing through a large window.

4.95 out of 5 average rating, 130 reviews

Beautiful Remodel in Sought After Wrigleyville

Modern comfort meets unbeatable location in this freshly renovated 1BR/1BA Wrigleyville gem. Enjoy the "new unit" feel with fresh paint, new appliances, and soaring 10-ft ceilings. Nestled in Lakeview, you're steps from top restaurants, bars, theaters, and iconic attractions. Perfect for travelers seeking style, convenience, and a true Chicago experience. Public transit is a block away and Spothero parking behind the building.

Popular amenities for Wrigleyville apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A vibrant living area features walls painted in pink, creating a lively atmosphere. A comfortable sofa, adorned with decorative pillows, is accompanied by two stylish chairs. A patterned area rug anchors the space, while a modern coffee table sits at the center. Natural light enters through large windows, framed by dark curtains.

4.98 out of 5 average rating, 65 reviews

Tickled Pink

The living space features exposed brick walls that blend with modern kitchen elements. A spacious light-colored couch is arranged around a round black coffee table on a patterned area rug. A wall-mounted TV is visible, alongside sleek kitchen appliances, enhancing the contemporary design.

5 out of 5 average rating, 38 reviews

Full Luxury Home in Wrigleyville

Apartment in Lincoln Square

A bright living room features hardwood flooring and a large, comfortable gray sectional sofa. Two unique yellow chairs are positioned nearby. A stylish TV unit and shelves display decor items, while light streams in through multiple windows, enhancing the open and inviting layout.

4.98 out of 5 average rating, 190 reviews

Vibrant & Chic Apt On Quiet St in Andersonville

A bright living area features large windows allowing natural light to fill the space. A brick fireplace serves as a focal point, complemented by framed artwork depicting cacti. Comfortable chairs and a wooden coffee table are arranged on a patterned rug, with a potted plant adding a touch of greenery.

4.95 out of 5 average rating, 61 reviews

Wrigleyville Oasis with Huge Garage

A spacious living area is framed by an elegant doorway, showcasing a comfortable blue sofa and light-colored armchair. Natural light filters through tall windows, illuminating a soft area rug on polished wooden floors. A round coffee table is centered between the seating arrangements.

4.86 out of 5 average rating, 86 reviews

Roscoe Flat 5 min walk to Wrigley Field

A comfortable living area features a cozy seating arrangement with soft cushions surrounding a wooden coffee table. A fireplace is positioned against a brick wall, with shelving displaying books and decorative items. An open kitchen is visible in the background, providing a warm ambiance.

4.98 out of 5 average rating, 87 reviews

Grace Place in Wrigleyville

4.93 out of 5 average rating, 230 reviews

A well-maintained garden unit is framed by a neatly arranged wooden fence. A covered porch with wooden railings offers a welcoming entryway. Snow blankets the small garden at the front, and the surrounding buildings display a mix of brick and stone facades.

Apartment in Uptown

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

A dining area is visible with a circular table covered by a festive red tablecloth. Four chairs surround the table. A comfortable couch is positioned against the adjacent wall, with light streaming in through the nearby windows. A decorative cabinet adds character to the space.

4.87 out of 5 average rating, 203 reviews

Lovely and Cozy Suite on Southport !

Private apartment rentals

Apartment in Lincoln Square

A bright living area is presented with a patterned armchair and a cozy sofa adorned with a colorful throw. A wooden coffee table is positioned in front, while a window with sheer curtains frames the view of the outdoor porch area.

4.95 out of 5 average rating, 409 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

A cozy kitchen and dining space showcases wooden cabinetry and modern appliances. Two patterned chairs are positioned around a round table, while a brown sofa adorned with colorful cushions adds comfort. Sunlight filters through yellow drapes framing a window, enhancing the inviting environment.

4.93 out of 5 average rating, 68 reviews

2 Room Apartment in Vintage Bldg

A modern studio apartment features a comfortable bed alongside a plush sofa. Large windows provide natural light, complementing the airy feel. A wooden table with stools is visible in the foreground, while a decorative rug lays across the floor, adding texture to the space.

4.95 out of 5 average rating, 56 reviews

Wrigley Designer Flat on Southport Corridor

Apartment in Andersonville

A red brick three-flat building is presented with large windows and intricate architectural details. Colorful pumpkins are arranged in the front garden, which features lush greenery and blooming flowers. A rainbow flag is displayed prominently by the entrance, adding a touch of vibrant color.

5 out of 5 average rating, 125 reviews

Andersonville 2 bed with modern kitchen + bath

Superhost

A spacious living area features a comfortable sofa and a light-colored coffee table. Columns frame an open archway leading to a dining space with a table and chairs. Natural light filters through large windows draped with grey curtains, highlighting the polished wooden floor.

4.72 out of 5 average rating, 318 reviews

HUGE unit, Wrigeyville, step to Wrigley, Metro

A modern living area features a black leather sofa and a wooden coffee table, creating a functional seating space. A large television is mounted above a stone fireplace, while a breakfast bar with several stools opens to the kitchen area, enhancing the home's communal feel.

4.99 out of 5 average rating, 86 reviews

Wrigleyville 2 bed 2 bath + Office Newly Rehabbed

A welcoming living area features a spacious gray sectional couch adorned with orange accent pillows and a coordinating blanket. A round coffee table sits atop a decorative wooden floor, complemented by an area rug. Natural light enters through nearby windows, illuminating the room's neutral-toned walls.

4.97 out of 5 average rating, 77 reviews

Charming Lakeview Oasis (parking included)

A modern kitchen space is highlighted by a large waterfall island with seating for six in teal, complemented by stainless steel appliances. Exposed brick walls add character, while pendant lighting illuminates the area, creating a welcoming atmosphere. Ample natural light enters through large windows.

4.96 out of 5 average rating, 74 reviews

Sensational 5 Bed beauty steps from Wrigley Field

Apartment rentals with a hot tub

Apartment in East Rogers Park

An open-concept living and dining area is showcased with a gray sectional sofa and a wooden coffee table. A modern ceiling fan hangs above, and natural light fills the space. A dining table with six chairs is positioned nearby, adjacent to a sleek kitchen.

4.85 out of 5 average rating, 101 reviews

Spacious Beautiful Condo

Apartment in Fulton Market

A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.

4.97 out of 5 average rating, 33 reviews

Skyline Oasis: City & Lake Views

Apartment in Near North Side

An open living area is highlighted by large, floor-to-ceiling windows overlooking the Chicago skyline. A light-colored sofa and modern armchairs surround a circular coffee table on a soft area rug. The kitchen features streamlined cabinetry and a breakfast bar, providing a functional space.

4.92 out of 5 average rating, 61 reviews

Prime Lincoln Park Views + Modern Amenities Await

Superhost

A spacious bedroom with large windows provides an expansive view of the city skyline. The comfortable bed is flanked by bedside tables with lamps, and art pieces are displayed on the wall. Natural light brightens the room, enhancing its modern aesthetic.

Apartment in Fulton Market

4.57 out of 5 average rating, 23 reviews

Level One Bedroom Suite | Fulton Market

4.97 out of 5 average rating, 38 reviews

The spacious bedroom features a queen bed and a cozy lounge chair. A light rug covers the hardwood floor, while glass doors open to a private outdoor space. A luxurious jacuzzi tub is visible in the bathroom, along with elegant tile accents.

Apartment in Wicker Park

Winter Escape 1 BR in Wicker Parl|1 FREE G Parking

4.97 out of 5 average rating, 147 reviews

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Apartment in Dunning

Belmont Pleasures - hot tub / arcade gaming room

4.91 out of 5 average rating, 57 reviews

A private balcony features wooden decking and a wooden railing. Two black wicker chairs with cushions and a matching coffee table create a cozy seating area. Potted plants hang from the railing, and the surrounding neighborhood is visible in the background.

Apartment in Albany Park

2Bed 2Bath 15min to Wrigley with Parking& Balcony